Triethylamine → [5-tert-Butyl-2-methyl-4-(toluene-4-sulfonylsulfanyl)-phenoxy]-acetic acid

HRID 1003877Notes

Reaction equation

HRID 1003877 reaction equation
[S:1](Br)([C:4]1[CH:10]=[CH:9][C:7]([CH3:8])=[CH:6][CH:5]=1)(=[O:3])=[O:2].CCN(CC)CC.C[O:20][C:21](=[O:36])[CH2:22][O:23][C:24]1[CH:29]=[C:28]([C:30]([CH3:33])([CH3:32])[CH3:31])[C:27]([SH:34])=[CH:26][C:25]=1[CH3:35]>C(Cl)(Cl)(Cl)Cl.C(Cl)Cl>[C:30]([C:28]1[C:27]([S:34][S:1]([C:4]2[CH:10]=[CH:9][C:7]([CH3:8])=[CH:6][CH:5]=2)(=[O:3])=[O:2])=[CH:26][C:25]([CH3:35])=[C:24]([CH:29]=1)[O:23][CH2:22][C:21]([OH:36])=[O:20])([CH3:33])([CH3:32])[CH3:31]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 101308854-Methylbenzene-1-sulfonyl bromideHCID 54427811(5-tert-Butyl-4-mercapto-2-methyl-phenoxy)acetic acid methyl ester

Product 1

HCID 18798672[5-tert-Butyl-2-methyl-4-(toluene-4-sulfonylsulfanyl)-phenoxy]-acetic acid

Reagents, catalysts & solvents 2

HCID 5943Carbon TetrachlorideSolvent2×HCID 6344DichloromethaneSolvent

Procedure

1.86 g (7.9 mmol, 2 equivalents) tosyl bromide and 1.05 mL (7.9 mmol) NEt3 were combined in 200 mL CCl4 and the mixture chilled in an ice bath under nitrogen. To this mixture was added a solution of 1.06 g (3.95 mmol) of (5-tert-butyl-4-mercapto-2-methyl-phenoxy)acetic acid methyl ester (prepared in Example MMMM) in 125 mL of CCl4 over 3 hours, and the reaction was allowed to come to ambient temperature overnight. The mixture was then diluted with CH2Cl2, washed with aqueous ammonium chloride and aqueous sodium chloride, and dried (Na2SO4). Concentration gave a residue which was chromatographed on silica gel eluting with 3:1 hexanes:EtOAc to yield the title compound. 1H NMR (CDCl3) δ 1.25 (s, 9 H), 2.14 (s, 3 H), 2.43 (s, 3 H), 3.82 (s, 3 H), 4.68 (s, 2 H), 6.75 (s, 1 H), 7.14 (s, 1 H), 7.25 (d, 2 H), 7.50 (d, 2 H).

Workup

  1. temperaturethe mixture chilled in an ice bath under nitrogen
  2. washwashed with aqueous ammonium chloride and aqueous sodium chloride
  3. dry with materialdried (Na2SO4)
  4. concentrationConcentration
  5. customgave a residue which
  6. customwas chromatographed on silica gel eluting with 3:1 hexanes

Sources & evidence

ORD record
ord-d2c309ac14a84669bf21ec772771f4c7
Source dataset
uspto-grants-2000_04
Patent number
US06046355

Reaction notes

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